CFLMMO,
I can offer some things to consider about Denver vs. Florida.
I understand the desire to live in the Denver area, or anywhere in Colorado for that matter. I too am feeling "stuck" in Florida, Tampa in fact, and I yearn to return to Colorado. I lived in Denver for 11 years from high school through several years after college. At that time, I was in need of a change and I came to Florida. I fell in love with it here (except for the humidity and bugs) and have been here for 18 years. But the love affair with Florida ended several years ago for multiple reasons and it's getting worse here every year.
Now, after vacationing in Colorado twice in the last 2 years--the first time I've returned since moving out in 1988--I've realized how much I miss it there. You can take me out of the mountains but you can't take the mountains out of me. My wife is ready to move there NOW and reminds me of this daily

. If I wasn't a "prisoner of my income" here, we'd be loading up the moving truck tomorrow. What stops me from having that moving truck here tomorrow is that we'd both have to quit our jobs and move out there with no new job secured. I can't bring myself to take that risk right now. My experience has been that long distance job searches are practically impossible and too expensive these days. You at least own a business and can employ yourself.
You're right on with the major negatives about Florida. Colorado isn't perfect, though. Even though I've not lived in Colorado for 18 years, I can offer the following points of consideration having lived there before (and I've been doing a lot of research lately on this very subject):
1. The cost of living is higher in Colorado than Florida, though the gap is closing with the aforementioned housing and insurance costs we're strapped with in Florida now. The cost of homes is comparable between the 2 states, but they're definitely higher in Colorado. However, it appears that the real estate taxes are lower in Colorado.
2. Colorado has a state income tax of 4.63% of your taxable income. Florida has no such tax. This does add up and should be considered if you're thinking of relocating there. Parts of Denver also have a local tax, though it's nowhere near the state tax percentage.
3. The cost of registering your car every year is substantially higher in Colorado than in Florida. Here I only pay $36/year for my license plates. Colorado would be about $300/year now, decreasing a bit as the car depreciates each year thereafter. This is something that would take me some getting used to (again). I'd feel like I was being robbed every year just renewing my license plates.
4. I'm not sure the average wages paid in Colorado are any higher than what we get in Florida, at least not in my field (payroll administration). With the state tax issue and the higher cost of living you better be making more in Colorado than in Florida or you'll feel the "squeeze." I'm sure this contributes to Colorado's very high foreclosure rate.
5. Car insurance costs about the same in both states, but homeowners insurance is less in Colorado for obvious reasons. I'll take the occasional short-term blizzard and mild tornado risk in Colorado over the widespread massive destruction of entire cities from major hurricanes that take many years to recover from any day.
6. Snow. And it gets cold in Colorado, something a person who's lived in the warm weather as long as you have will find that it takes time to get used to. The good news is that it doesn't snow as much in Denver as people think it does. And it doesn't stay on the ground for months on end like it does in, say, Michigan (speaking from experience).
I'd take the "negatives" of Denver over the negatives of Tampa any day. Best of luck if you make the move. Wish I could say we were doing the same.